Some celebrities couples make having a huge age gap work. George and Amal Clooney, Catherine Zeta-Jones and Michael Douglas, Sarah Paulson and Holland Taylor, and Jason Momoa and Lisa Bonet, to name a few.
But other couples don't work out so well. There will always be older men in Hollywood who divorce their wives of however many years to date younger women, close in age to their own children. Those relationships hardly ever work out. Ewan McGregor's daughters hope their father's affair with Mary Elizabeth Winstead burns, just as Paul McCartney's children thought the same after he married Heather Mills.
The same can be said for Sean Penn's daughter, Dylan. After divorcing Robin Wright once and for all following their on-again-off-again 20-year relationship, Penn dated around until he started seeing fellow actor Vincent D'Onofrio's daughter Leila George in 2016. Penn and D'Onofrio are both 61 years old, while Leila is 29. They married this past year. That's practically like marrying one of your parent's co-workers.
Guess Penn and his other ex, Madonna, are similar in the way they date nowadays. Here's the story about Penn's relationship with his younger wife and what her famous father has to say about it.
Leila Grew Up On Her Parent's Sets
Being the daughter of veteran actors D'Onofrio (Men in Black, Mystic Pizza, Law, and Order: Criminal Intent) and Australian actress Greta Scacchi (Presumed Innocent), Leila reaped the benefits of having famous parents. Like Penn's own children, she grew up on most of her parent's film and television sets.
"Growing up, I'd sit on my mum's or dad's sets for hours and hours and not get bored. That's always where I wanted to be," she explained.
So it's no surprise that she wanted to go into the family business. But she was scared at first. She called her dad for advice on what she should do, and he asked her what she was afraid of. She said acting, so D'Onofrio said, "Well, that’s what you’ve got to do."
She went on to study film at the Arts Education Schools, London, Sydney Film School, and also attended Brighten and Crawley Colleges. Then she enrolled at New York's Lee Strasberg Institute, where her father teaches a master class.
She made her feature film debut in Mother, May I Sleep With Danger? in 2016 and star in films like Mortal Engines, The Kid (which her father directed), and the series Animal Kingdom.
It wasn't hard to imagine that Leila would follow in her parent's footsteps. What is hard to imagine is that she somehow crossed paths with Penn at some point in 2016 and decided to date him.
She Has An Interesting Ride Ahead Of Her
More than likely, Penn met Leila through their mutual love of charity work. After first being spotted together making out on a beach in 2016, they've kept their relationship extremely private.
But they have appeared at a couple of charity events. They were seen at the "Meet Me In Australia" event, which benefitted wildlife relief in Australia, and later teamed up to help COVID testing facilities. They've also been spotted hanging out with another couple who has a huge age gap, Leonardo DiCaprio and Camila Morrone.
According to the Daily Mail, Penn confirmed their relationship on the Howard Stern Show in June 2020. He said Leila was the "gal" in his life and explained that he could sometimes be difficult to be with. Apparently, Leila is capable of handling him.
"Am I difficult? Yeah, I think so. I will say I'm a person who feels and expresses energetically; I've misled people into thinking it's all about me. I think the interview you're talking about would be a lady named Leila George; she knows me better than I do on this level, that doesn't mean I agree with her perceptions, but I certainly find them fascinating," he said.
One month later, rumors that they'd tied the knot started to circulate after a friend posted a congratulatory message on a since-deleted Instagram post.
"We are so happy for @leilageorge #seanpenn getting married. We love you. We are over the moon to find your soul mate true partner. You are meant to be together God Bless you both," philanthropist Irena Medavoy wrote on her Instagram.
Penn later confirmed it on an episode of Late Night with Seth Meyers.
When asked about the marriage rumors, Penn raised his left hand to show his new golden wedding band and explained, "We did a COVID wedding. By that, I mean it was a county commissioner on Zoom, we were at the house, my two children and her brother, and we did it that way."
Judging by Penn's comments about their relationship dynamic to Stern, it sounds like the young bride will have her work cut out for her being married to Penn. He was previously married to Madonna from 1985 to 1989 and married to Wright from 1996 to 2010, and both of those marriages ended messily. Both Madonna and Wright filed for divorce, retracted it, then filed a second time successfully without reconciling with Penn. There were even rumors of domestic violence during his relationship with Madonna.
So this, of course, can't be sitting well with D'Onofrio, who, as we heard from Penn, did not get to walk his only daughter down the aisle and who wasn't even at her Zoom wedding. He also can't be pleased to call Penn his son-in-law.
But it looks like they are all on speaking terms, at least. During the lockdown, D'Onofrio posted a joint video of himself playing the Ukulele with Leila, filmed from their separate lockdown corners. "Having a lil long-distance fun. Love you my daughter," he wrote.
D'Onofrio also tweeted that he agreed with Penn that "Masklessness is an anti-American tattoo," so it would seem as if he at least agrees with his new son-in-law on one thing. Whether or not he agrees with his little girl marrying a man his own age remains to be heard.